Enantiomerically divergent pathways in Tsuji-Trost reactions: exploiting the structural differences between β-acyloxy-o-(diphenylphosphino)benzamides and β-amido-o-(diphenylphosphino)benzoates

Add time:08/28/2019    Source:sciencedirect.com

Using a single chiral scaffold, (1R,2S)-norephedrine, a series of monophosphine ligands have been prepared. The ligands prepared, β-acyloxy-(o-diphenylphosphino)amides and β-amido-(o-diphenylphosphino)esters, give rise to enantiomerically divergent products in the Tsuji-Trost asymmetric allylic reaction. The phosphinoamides afforded the best enantioselectivities and favored the (S)-enantiomer of the product. In contrast the phosphinoesters afforded lower enantioselectivities and favored the (R)-enantiomer. A mechanistic rationale for this observation is proposed.

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